I Am A Factory Girl
by Alice in Wonderless Land
Summary: "Damon had promised himself No More Teenagers... Jenny was different. She knew who she was. She was an old soul." AU Jenny/Damon, set in the 'future'. Rated M for sex, drugs and rock and roll but mostly sex .
1. Let's do something to regret

_Two YouTube videos, five Fan Pics and several crazy pills later and Jenny/Damon is suddenly extremely appealing to me in terms of Crack Pairings. I don't even know what I'm doing..._

_Alice_

_P.S. Don't worry about 'I'm not a drinker, I'm a drunk' because this is just a little procrastinating side-project. Chapter eight of 'I'm not a drinker, I'm a drunk' will be up soon._

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Chapter One: Let's do something to regret.

* * *

New York City was always one of Damon's favourite places in the world. He had been everywhere – pretty much – and somehow he always found himself in New York because, hey, why not? The city never slept and neither did he, so it was a match made in heaven.

Although, since the whole Mystic Falls schtick two years ago, he had become very... humanised. To say the least. He slept a whole eight hours some nights, which was even more ridiculous when you consider that his kind usually slept during the day.

Through word of mouth he heard about some throwback burlesque club called _Victrola_. Soon enough he found himself in what could only be described as a retro escapist strip club. See, this was why he liked New York. It was so much better than The Grill back in Mystic Falls where the prime entertainment was pool and annoying cougars. Yes. This was much better.

Damon settled himself into one of the plush couches and a scantily clad brunette in nothing but a corset and stockings offered him a drink. He asked for a scotch – no, make it a double. Then he made himself comfortable and observed his surroundings. He had just eaten that morning (a very eager waitress at the corner diner left him her number, so he had tasted and compelled her when she went out for a cigarette break) but all of these girls were quite exceedingly attractive. Of course, they were slathered in red lipstick and covered in perfume that marred their natural blood-lust inducing scent, but they were still appealing.

Damon was on his second scotch when she walked in. She was being tailed by two other girls and didn't look a day over eighteen. He wondered briefly how she was even allowed in before a young man (who he had previously recognised as the owner) came up and greeted her, giving her a chaste and polite kiss on the cheek. That explained it. The friend of the boss doesn't need I.D.

She and her cohorts slid into a booth near Damon. The leader – a tall, pretty blonde with dark eye makeup and long legs – had a sour expression on her face while her two friends giggled and pointed around the club. They had clearly never been there before. The leader nodded to her friends and offered them a small, half-hearted smile and they ran off to go get drinks. She was all alone. Ripe for the picking.

Damon didn't approach her. In the fifteen minutes they had been there she had already been hit on three times and all of those men – no matter how young, attractive or wealthy – were turned down with a pursing of her lips and a raise of one slim eyebrow. Instead, Damon thought, she would come to him.

Vampires are predatory, but subtle. They are built to attract their foes and be alluring. It had something to do with endorphins, although Damon never cared enough to find out the exact details. He had no doubts that her eyes would find him sooner or later.

And when their eyes did meet, it was an explosion. Her dark blue eyes met his bright azure ones and he saw her take a sharp intake of breath. Of course she did. She wasn't expecting the intensity of his stare or the allure of his very presence.

It was perfectly normal.

What he didn't expect was the way she pursed her lips at him – at _him_ – and turned her head away.

Oh, it was so _on_.

When her friends got back, they noticed him staring at their leader. They giggled, the way teenage girls often do, and pointed him out. Over the music of the club, Damon could still hear them.

_That hot guy over there is totally staring at you, J!_

_Yeah. What of it?_

_He's so fine! We think you should go over and speak to him._

_He's just being a pervert._

_Oh my god, J! Please go talk to him or I will._

Then the leader – named 'J' for some reason – let out a resigned sigh through her red painted lips and rolled her charcoal smudged eyes. She rose from her seat, all long limbs in a short dress, and made her way over to Damon's table. He didn't take his eyes off of hers until she was right in front of him, staring him down.

"Hello," he said smoothly, raising an eyebrow. The girl didn't blink, she just let her lips curve into the slightest approximation of a smile.

"You're staring at me."

"Was I?"

She looked away in obvious frustration with his attitude. She was used to people following her every move. She was used to being the Queen.

"I'm Jenny. Jenny Humphrey," she introduced herself.

"Bond. James Bond," Damon mocked, taking a sip of his scotch. Jenny huffed and let out an uncontrollable smirk.

"I know the owner, you know. I could have you kicked out."

"Damon," he replied. "Salvatore."

Jenny took his real name as an indication that she was welcome to sit down. She sat down on the lush sofa beside Damon and called over a waiter, ordering a gin and tonic.

"Aren't you a little young to be drinking?" Damon queried, cocking an eyebrow again.

"Aren't you a little old to be hitting on eighteen-year-olds?" she asked as she sipped her drink.

"You have no idea."

Later that night, when the gin and scotch was swimming in their respective systems, Jenny agreed to let Damon come home with her. He had no place to stay as he was only there for the night and had to be off soon. Katherine was in New York and he desperately needed to avoid bumping into her, though that wasn't what he told Jenny.

She had just nodded at him. She had an apartment on the Upper East Side in a hotel building. He knew her family must be rich but she didn't reply when he commented on it. In a slur, she simply mumbled...

"Ever been to Brooklyn?"

Even in his drunken state, Damon took in every inch of her small but lush apartment. There was a mannequin in the corner and textbooks with F.I.T written on them in big letters. Fashion Institute? He was piecing together Jennifer Humphrey's puzzle and it seemed a large one.

He didn't get much time to think, though. Because Jenny hooked her fingers into the buttons of his shirt and brought him close to her. Her sweet, gin scented breath tickled his face before she lowered her mouth onto his. Then he could taste her. He tasted her last cigarette, her gin and tonics, her chocolate strawberry snack, her dark red lipstick. Her tongue swiped the inside of his mouth, trying to taste him, too. What would she taste? His scotch, his death, the blood of the waitress he had that morning?

Damon had promised himself No More Teenagers. Caroline Forbes had thrown herself at him and Elena... well, Elena had been something else entirely. What they both had in common was an unparalleled innocence about them that made him uncomfortable. He wasn't the 24 he looked. He was over 160 and he felt it in his bones and teenagers were so gangly, and awkward and trying to find themselves.

Jenny was different. She knew who she was. She was an old soul.

He could taste that on her, too.

When she undressed she was wearing a garter belt, which made Damon chuckle. She took off her high-heels and suddenly became shorter than him and her dress was over her head. She was pale in the moonlight, milky white skin that glowed in the dark. Damon removed his clothes and manoeuvred them to the bed. She smelled of gin and Chanel Number Five.

He kissed down her translucent flesh and could feel her pulse under her skin. But he was far more aroused than hungry and instead guided himself inside her while she moaned and bit down on his shoulder softly. He rocked and she moaned breathily and low, her black fingernails digging into his back and leaving half-moons in his flesh.

When he finally climaxed after what felt like the most long-lasting and intense sex of his un-life, Damon felt Jenny clench and orgasm around him, quivering with pleasure as she rode him off the edge.

Afterwards, they lay there. Damon wasn't asleep, though he was exhausted. He could feel the light coming in through the window. It was almost morning. How long had they been going at it? He wrapped his arms around Jenny's thin waist and listened to the sound of her steady breathing. He played games with her breathing – trying to make them breathe in sync, in canon. He made patterns with their breaths and inhaled her.

Damon was not a romantic.

Sure there was _love_ and _puppies_ and all that boorish nonsense, but he didn't believe in soul mates. He didn't even know if he believed in souls. But when he awoke without recognising that he had gone to sleep and found her gone, he felt a pang of disappointment. Girls didn't skip out on him. He was Damon fucking Salvatore! He bled girls dry and left them braindead and they most certainly enjoyed it.

He got up, slipped on his boxers, and exited the bedroom to take a good look around the apartment. On the windowsill was an ashtray with a few butts in it. Fresh, new from his morning. She had only left a few minutes ago. He moved over to the kitchen and saw a post-it on the fridge.

_Damon (if that is your real name),_

_I had to go to class. Help yourself to anything in the fridge, though I know you probably didn't need permission._

_J_

He laughed aloud at the note. She was awfully flippant for such a young girl. Did she do this often? Drag drunken strangers into her apartment, have her way with them and then leave behind a post-it? Damon opened the fridge and pulled out some leftover pizza, though he knew that the dull aching throb in the back of his throat wasn't a regular kind of hunger. He looked at his watch absently and decided to see if any of the Victrola girls had slipped him their phone number...

* * *

When Jenny got home from class, it was almost dark. She sighed and threw the samples she'd made in Design over a chair in the living room before making her way to the kitchen for some water. On the fridge, underneath her mandatory 'Thanks For The Fuck' post-it was another note.

_Jenny (if that is your real name),_

_I'm thinking of staying in New York. Look me up at Victrola._

_Damon_

She resisted the urge to smile. Damon Salvatore was most definitely one of the most charming and good-looking people she had ever met. But it was an uneasy charm, something dangerous about it. Distantly, her mind recalled Nate Archibald and his easy charm which had something more to do with his family, his money, his green eyes, his easy smile and his flicky hair. No, Damon Salvatore had another breed of charm altogether. An animal charm.

Jenny immediately had the impulse to grab her coat and head down to Victrola and start the whole act again – the staring, the drinks, the sex. But she thought better of it and instead whipped out her mobile and tapped in a quick text.

_You know that guy I left with last night? X J_

While she waited for a reply, she wandered around her apartment before winding up at the windowsill. She reached into her bag to light a cigarette, but stopped when she saw the ashtray. It was filled to the brim with cigarette butts and there was a post-it hanging off of it as well.

_They'll kill you. – Damon_

Jenny just laughed and lit her cigarette, briefly pondering the point of chainsmoking a whole pack just to prove a point. She was halfway through her cigarette when her phone buzzed.

_Indeed I do. Being nasty, are we? –C_

Jenny rolled her eyes and replied to Chuck's text.

_He said he'd be at Victrola tonight. Keep an eye out, will you?_

The reply was instant:

_Of course. Any particular message you'd like conveyed?_

Jenny thought for a moment, taking a deep, long drag on her cigarette.

_No. Just tell me when he leaves._

Jenny got changed out of her school clothes – flats, skinny jeans, a singlet and her hair in a long plait – into her more signature style. She had spent most of her teenage years running up and down the Upper East Side in 5 inch heels and tight dresses. Starting at F.I.T had meant that she had to be more practical, which wasn't something she enjoyed very much. She casually made her way to her closet before deciding on a short black dress, lace stockings and a pair of Steve Madden pumps. She then shook out her long, white blonde hair and picked up a Burberry coat.

Hanging out with Blair wasn't something she did often, or very willingly, but they had maintained a strained friendship since Blair got over the whole You-Slept-With-Chuck thing and Jenny had wised up and become less of a brat. Meeting at the hotel bar to bitch was about as close as they got to being teenagers in the Constance Billard hierarchy again, though they weren't particularly fond memories for Jenny.

Blair was waiting for her at the bar, as usual, tapping on her phone and sipping on a martini. When she saw Jenny approach, a smile quirked on her lips and she sighed.

"You're just a little slut, aren't you?"

Jenny rolled her eyes. It wasn't the usual greeting, but it was the usual animosity she expected from Blair.

"Yes, Blair. I'm a bit fat slut," Jenny sat beside her at the bar and just ordered water. She was still trying to get all of the gin and tonic out of her system from the night before.

"I'm talking about Gossip Girl, J," Blair sighed and flashed her phone at her. On Gossip Girl's page, there was a picture of sitting at Victrola with Damon, a picture of her leaving with Damon and a picture of her letting him into her apartment building.

Creepy.

"What, so now I'm not allowed to have a social life?" Jenny queried, raising an eyebrow.

"J, you can't have one-night-stands. It's really not good for your reputation."

"It wasn't a one-night-stand," Jenny defended herself automatically, frowning.

Blair was silent, before tucking a strand of chocolate hair behind her ear and lifting her chin in interest.

"Oh, really?"

Jenny bit her lip slightly, thinking of how to reply. "His name's Damon. He's... older than me," she conceded.

"How much older?"

Jenny was about to say 'I don't know. Early to mid twenties?' but that would have supported the one-night-stand theory that Blair was (correctly) sporting, and she didn't want to admit that she didn't know him well.

"Twenty-five," Jenny said, before deciding to elaborate, "Well, almost. His birthday's coming up."

Blair probed even further, taking a deep sip from her martini.

"Last name?"

"Salvatore."

"Italian?"

"His family is."

"Lives in New York?"

"No."

"Then where?"

Jenny had to think. Back at Victrola she had asked him that same question. And the answer she'd received was as mysterious as he was – 'I don't have a home'. But then she'd asked where he came from and he said something about a nosey little town called Mystic Somethingorother. She couldn't remember.

"A town called Mystic. Very small," she settled on, knowing full well that Blair would do a raincheck on any and all towns with the word 'Mystic' in them.

Blair just nodded and said in her usual, clipped tone, "Well, the Fashion Week Fundraiser is tomorrow night. You should bring him. Introduce him to everyone."

Jenny began to stammer, "Uh, I don't think we're at that point yet, B. I mean, really we've only been seeing each other-"

"So he's good enough to sleep with but not good enough to meet your friends and family?" Blair questioned, knowing that Jenny couldn't argue with that one.

Jenny just forced a smile and said, "I'll ask him."

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**Reviews = love.**


	2. Elvis and Suicide

_Nobody's reading this anyway, so why not procrastinate and write another chapter?_

_X Alice_

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Chapter Two: Elvis and Suicide

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Damon idly fiddled with the ring on his finger. The sunlight was streaming through the window of the same corner diner he had eaten at his first morning in New York, casting his face in a warm glow. The waitress came up to him with a smile, and he noted with some kind of satisfaction that she was still wearing the little scarf he had told her to put on. The bite marks were completely concealed.

"Freshen your coffee?" she asked, oblivious to their prior encounter.

"Please," Damon raised his eyebrows and pushed his mug in her direction.

The previous night at Victrola had been disappointing, to say the least. He had been unwilling to get drunk and while he happily fed off of two of the dancers, he didn't sleep with either of them. He simply hadn't wanted to. And, it was also disappointing due to the fact that Jenny hadn't come to find him.

But of course not, he reasoned. She probably didn't want to seem desperate. Although she most probably was.

Damon reached for his wallet to pay for his breakfast, but found his pocket empty.

"Shit," he muttered. He could always compel the staff into thinking he'd payed, but that wallet was brand new, Italian leather and was worth more than several breakfasts. His urge to find it had _nothing_ to do with the fact that a picture of Elena was tucked gently into one of the folds.

Nothing at all.

Damon made his way to Victrola after 'paying' for his breakfast. He must have left it there because it was the only place he had been other than Jenny's apartment, and he knew he had it on him when he left there.

Of course, the club itself was closed. But the bar was open and a young man in a suit, the owner he recognised from two nights before, was speaking to the bartender. Even if they weren't open for business, Damon had no doubt that they would be willing to let him in and search for his lost wallet.

As he entered, the young man in the suit turned and looked at him with narrowed eyes.

"Can I help you?" the young man smirked.

"I left my wallet here last night," Damon explained.

The young man reached behind the bar and revealed Damon's neat, dark brown Italian leather wallet. He opened it and looked at the driver's licence that Damon had renewed the previous year. It payed to have as much documentation on file as possible, he had learned. People often snoop without you being there to compel them into thinking otherwise.

"Damon Salvatore," the young man read aloud.

Damon reached for the wallet, but the owner of the club didn't return it.

"I believe you've met my step-sister," the owner drawled in a low voice. "Jennifer Tallulah Humphrey."

Damon suppressed a snort. Tallulah? Really? Instead, he just nodded and let a smirk play on his lips.

The young man smiled and straightened his back, handing the wallet over finally. Damon took it back and looked through it. Credit cards, money, I.D. All there. He briefly checked to see whether the photo was still in place, but only took it out enough to see the corner of Elena's dark brown hair.

"Does Jenny know about her?" the young man asked.

"Who?"

"The girl in the picture."

Damon looked up and was about to ask something along the lines of 'You went through my wallet?' but instead he just shook his head.

"It's not like that," Damon assured the man in the suit.

The young man nodded and said in a low voice, "I should hope so. She told me to give you this."

It was a phone number written on a post-it, folded neatly in half. Damon took it from the man in the suit before finally allowing himself to laugh.

"Who are you?" he managed to ask.

"I'm Chuck Bass."

* * *

Jenny was pacing around her apartment with a half-smoked cigarette in her fingers. He would call, wouldn't he? Chuck had said he left his wallet there the night before, so when he went back he'd get her number and he'd call. He had to call.

Not that she was hung up on him or anything. But she really needed his help if she was going to maintain some dignity. The whole Upper East Side Bitchfest had never been her cup of tea, but no matter how hard she tried to deny it, it was a part of her. And Gossip Girl, and her family, and her friends would always be preoccupied by her life's scandals.

Damon was simply the latest bump she had to smooth.

She looked at her watch and saw the time. Almost noon. She had to go to her afternoon classes soon, but he had to call first so she could explain about the Fashion Week Party and how he simply had to come with her and pretend to be her legitimate boyfriend because otherwise she'd be forever known as the Hotel Harlot, or whatever. And she really did _not_ need another black mark on her reputation, especially when she had only just reaffirmed her position as Queen of the F.I.T clique.

She was about to light her third cigarette when her phone buzzed in her back pocked. She quickly reached for it and checked the number – unknown. Of course. Damon always had to be mysterious, didn't he?

Jenny took a deep breath to calm herself before answering.

"Hello?"

"Tallulah, huh?"

She practically hear his smirk on the other end. She could also hear cars. He was on the street. _Duh, _she told herself, _he has nowhere to stay in the city_.

"You should feel privileged," she replied. "Not many people know my middle name."

"Oh, I feel privileged, alright."

Jenny let out a breathy laugh, before cutting to the chase. "I need you to do me a favour."

There was a pause, before Damon replied, "What would this favour entail?"

"Wearing a nice suit and escorting me to a party filled with rich snobs," Jenny explained.

Damon laughed, and Jenny continued, "I know this is out of the blue..."

"Yeah," Damon stated, "usually I escort the pretty girl to the party before I sleep with her. But whatever. You're unconventional."

Jenny huffed a little, rolling her eyes, though she knew he couldn't see her.

"Is that a yes?"

"It's a yes."

"Do you need me to get a suit for you, or...?"

Damon laughed again. "I think I can handle that part. What time should I meet you?"

"Do you remember where my place is?"

"Yep."

"Meet me there are around 7."

"Sure thing."

"Also," Jenny added as an afterthought, "You're my boyfriend, you're desperately in love with me, and we've been seeing each other for several weeks, now."

And with that, she hung up.

There was silence in Jenny's apartment for a few moments, only broken by the sound of taxis hooting out her open window. She was expecting him to call back, to question the last part that she had simply thrown in there. But he didn't. She supposed he just accepted it. Jenny sighed and quickly flipped to Gossip Girl's website on her phone.

_Gossip Girl, here, your one and only source into the scandalous lives of Manhattan's elite._

_Fall means new wardrobes, new businesses and Back To School for the younger ones among us. __**Little J**__ is back at F.I.T and rocking it all the way to Sunday, while her older brother is holed up in his apartment, writing his little heart out. Maybe something will be published this season, huh, __**D?**__ Likewise, __**S**__ was spotted job hunting again. That girl holds a job worse than she holds onto a man. But we can't complain, because each one of us would simply love to be walking in her shoes (or in this case, in her brand new Chanel boots). __**B**__ is back from Paris, looking incredibly refreshed and lovely.__** N**__ is nowhere to be found. Maybe his summer in the Hamptons was so good he didn't want to come back. And __**C**__? He's back in business with his sleazy little club. In fact, __**Little J**__ was seen leaving there two nights ago with a mystery man. Perhaps she's up to her old tricks, huh? And here I thought that she had turned over a new leaf. Oh well, I guess only the seasons ever truly change._

_You know you love me,_

_xoxo Gossip Girl_

As much as Jenny hated it, Gossip Girl still got to her as much now as it did when she was fourteen. But, if all would go to plan, everyone would see that she had turned over a new leaf. Or at least, that's what they'd believe.

* * *

With fifteen minutes to get ready, Jenny had decided on a deep red Elie Saab mini-dress. Last season's collection, but still wearable. She pulled on black stockings and was applying lipstick that matched the colour of the dress perfectly when there was a knock at her door. Probably Damon, she assumed, and with a quick pop of her lips to smear around the colour, she moved from her bathroom to the front door.

When she opened the door, she was taken aback.

She had known and remembered Damon's good looks, but this didn't even compare. He was wearing a solid black suit, with a black collared shirt under it. No tie. It looked perfectly tailored to his firm build and she had to keep herself from staring. His dark, almost black hair was combed back and he was looking at her with an amused expression in his light blue eyes, almost as if he were laughing at her silently.

"You weren't expecting me to look this good," he surmised, cocking an eyebrow at her. Jenny closed her mouth and smiled.

"Whatever. Let's go."

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**Reviews = much love.**


	3. I'll drink what you leak

_Chapter three is up and running._

_This is so not like 'I'm not a drinker, I'm a drunk.' I mean, don't get me wrong, I love writing that. But it's so constrained to the world of the TV show. I guess AUs and crossovers just give more freedom. Also, if nobody reviewed 'I'm not a drinker, I'm a drunk' I doubt I'd keep writing it. But 'I Am A Factory Girl' just sort of writes itself, I guess._

_X Alice_

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Chapter Three: I'll drink what you leak

* * *

Damon was used to playing this part.

Even as the years went by, he was always roped into some sort of lavish formal event that meant he needed good suits, a lot of money and a dazzling smile. Good thing he had all three, although Jenny didn't seem to realise it. She probably thought he was some unusually attractive, but incredibly poor stranger from some little town in Virginia. Oh, how she was mistaken.

"We should get our story straight," Jenny said, tucking a strand of long, white-blonde hair behind her left ear. Damon resisted the urge to roll his eyes, remembering that this girl knew nothing about him. Hence, she knew nothing of what a fantastic bullshit artist he was.

"I can handle it," he assured her with a laugh.

"You moved here from that town place, like a month ago," Jenny continued, as if deaf to his assurance. "And we met each other, instantly fell in love, and we have a fantastic but incredibly moral relationship."

Damon simply had to snort at that. First of all, 'fell in love'? Even that sounded too farfetched, let alone the 'incredibly moral' part of their supposed 'relationship'. Damon shook his head at Jenny's distraught face and put his hand on her knee.

"You're underestimating my fantastic bullshit abilities," he raised his eyebrows slightly and gave a smile. Jenny just tipped her head to the side slightly, probably wondering about how little she really knew him. Well, she obviously knew how devilishly handsome he was, and how great he was in bed. But beyond that, he remained a mystery. And he liked it that way.

"Okay, well, in case anyone asks you," he sighed, "I am from Mystic Falls, Virginia. An old, old family, dating back to post-civil war Italy. Old money."

Jenny raised her eyebrows in surprise, but didn't interrupt.

"I moved here because I'm..." Damon thought for a second, "trying to get into a business."

"What business?" Jenny probed with a smile. Damon just glanced over to her.

"I have no idea _what_ I'm getting into."

* * *

As the pair stepped out of the black town car, they were immediately greeted by staff and the lovely people from Page 6. What Damon hadn't been expecting was the flashing of cameras and the calling out of, "Jenny! Jenny Humphrey!" as they made their way to the entrance.

"You didn't tell me you were famous," Damon said, only half joking with a quirk of his eyebrows. Jenny simply scowled, an expression he hadn't seen since that first night at Victrola.

"In this world I am," she said grimly, before looping her arm in his and plastering a smile on her face.

As this was a Fashion Week event, there were models standing around in avant garde fashion, simply posing and staring off into the distance like flesh-mannequins. The music was 'hip', but inoffensively loud, seemingly to accommodate the older attendees.

Jenny searched through the crowd. She had to find someone – anyone – and prove to them that the 'mystery man' wasn't such a mystery. She dragged Damon through the surges of well-dressed people as politely and elegantly as she could in five-inch heels, before finding her first friend.

Unfortunately, that first friend was Nate Archibald.

"Jenny?" Nate turned to her with a furrow of his eyebrows and an easy smile.

"Nate!" Jenny tried to sound excited instead of surprised. Hadn't Gossip Girl just said that he was MIA?

They shared a polite, European kiss on each cheek, before Jenny had the sense to introduce Damon to him. That was the whole point, wasn't it? She couldn't be distracted by him.

"Nate, this is Damon Salvatore," she said politely. She watched the two shake hands and inadvertently compared them to one another. Similar heights, completely different colouring. Damon's fair skin clashed with Nate's honey-tanned smile. "Damon, this is Nathaniel Archibald."

Nate smiled at the sound of his full name, like it was embarrassing. Jenny was about to get into a panicked tirade of she and Damon's fantastic romantic history, but was cut short by a familiar voice.

"Jennifer," Chuck drawled.

Damon opened his mouth, as if he were about to say hello. But Chuck interrupted him. "Who is this fine young man?"

Jenny let out a silent sigh of relief, mouthing a quiet Thank You to Chuck. He just nodded, and the introduction began again. She only hoped that Damon wouldn't get tired of being introduced.

* * *

Damon was getting tired of being introduced.

He had met a total of seven of Jenny's friends. Individually. That meant seven 'ohmygod, _hi_'s and seven 'Have you met Damon? This is Damon Salvatore's and it was getting on Damon's nerves. He grabbed a drink as quickly as he could, but all they were serving was champagne and he _loathed_ champagne. Wasn't there a bar, or something?

"I'm sorry," Jenny whispered to him as they fended away two girls named Kati and Isabelle, whom Damon had absolutely no interest in meeting.

Eating, maybe. But not meeting.

Damon just took a slow, deep, unnecessary breath. "It's fine," he whispered back, getting as close to her as possible so that she would feel the warmth of his breath on her neck.

"I'll get you a drink," she smiled. "Scotch, right?"

"Make it a double," he cringed at her and she laughed, heading off towards the bar.

Damon was tempted to get out his phone and start texting Stefan, or Elena, or somebody about what a ridiculous situation he was in. A lot of the younger people around were typing on their phones furiously, so he didn't think he'd be out of place doing so. Before he could even reach into his pocket, a brunette girl walked up to him with a smile.

"You must be Damon Salvatore," she said in an easy, albeit clipped tone.

"You have no idea how thankful I am that you know my name," Damon leaned in and said in a hushed voice. The brunette girl tittered a little bit before cocking her head to the side and thrusting out her hand to shake.

"I'm Blair Waldorf," she introduced. "A good friend of Jenny's."

"A pleasure," Damon replied, shaking her hand gently, but with a firm grip. With a small, confused smile, Blair held his hand up and straight.

"Um. Nice ring," she commented, half sarcastically.

"Garish, isn't it?" he smiled. "Family heirloom."

The ring glinted in the swirling lights of the party, and Blair stared at the family insignia. A smirk crossed her lips slowly and she tilted her head to the side.

"The Salvatore family goes all the way back to Italy, right?" she asked, although she already knew the answer.

"Yes," Damon replied. "My great, great, great grandfather was Giuseppe Salvatore, and he came over from Italy in the eighteen hundreds."

"To Virginia," Blair added, sounding absolutely sure. "Mystic Falls."

Damon frowned a little, but nodded. This girl had obviously done her research. He wondered how much she had been able to dig up...

"Giuseppe actually helped found the town," Damon said with slight irritation edging his voice. He never did like talking about his father, especially when he had to make him not sound like the ass he really was. But Blair didn't notice, she just smiled and nodded. He assumed she was one who was easily drawn in to 'Old Money' and stuff like that. Maybe she could trace her family back to the Mayflower or something just as ridiculous...

The usual interrogation ensued. How long have you and Jenny known each other? How long are you staying in the city? Blah, blah, blah. But Damon liked Blair. She asked because she was trying to dig deeper. It seemed like something he might do, if he were in her position.

Jenny soon approached Damon from behind and gave him his scotch. He smiled at her, and thanked her politely.

"Have you met Jenny's dad?" Blair asked slyly with a cock of her head. Damon's eyes instantly widened. Meeting the parents? It wasn't something he ever liked, especially when said parent couldn't be swayed by his good looks and charm – i.e. fathers. Couldn't he meet her mother, first?

Jenny just laughed it off and said, "Rufus isn't even here tonight. Maybe I can find Lily somewhere..."

Rufus and Lily? Damon could sense the animosity coming off her in waves, as it often did when children called their parents by their first name. He wanted to know more of the back story, but Blair interrupted his thoughts with a question...

"Have either of you seen Chuck?" she asked, a hint of desperation in her voice.

This time, Jenny's eyes widened.

"He's right over there," Damon said with a smile. Only after Blair trotted did he understand what Jenny's reaction was. And, he only understood once she elbowed him in the ribs. He made a show of acting winded, only with a smile.

"What was that for?"

Jenny scowled. He could sense this was becoming a trend...

"Chuck? As in _the only person who has the ability to make me out to be a whore_?" she whispered fiercely.

Damon rolled his eyes. "Don't worry about it."

"How am I supposed to not worry about it?" she whispered again, loud enough that the act of whispering seemed superfluous to Damon. "He knows that the first time I met you was the other night. And he tells Blair everything. He has to, now."

Damon was about to ask what the last part of her tirade _meant_, but instead gave her an easy smile.

"Believe me. He's not going to say anything," Damon quirked his eyebrows and cast a glance over to Chuck Bass, who was smiling at Blair as she waltzed up to him. No. Chuck wouldn't say anything. He didn't even remember anything.

* * *

_Gossip Girl here, your on__e and only source into the scandalous lives of Manhattan's elite._

_Did you hear? __**Little J**__'s new beau is actually a new beau! And here we were thinking she was up to her old tricks. But it's been confirmed by numerous sources. The new couple is very much in love. And did any of you girls catch a glimpse of Mr Tall-Dark-And-Handsome? __**J**__ might have a sketchy history, but her taste certainly hasn't felt any adverse effects. Also, __**N**__ showed up out of nowhere for Fashion Week! A few sources say he was staring intently after __**J**__ like a dog with a bone, but that's probably just the jealousy talking. __**S**__ was there, too, cosy with her new boss. Wonder how she got that job?_

_**D**__'s also scored himself a job (finally). Apparently, our own little Williamsburg film prodigy wants to make a film about him! __**V**__ was spotted with her camera at the writer's loft apartment in Brooklyn. Or maybe they're doing something a little naughtier?_

_**B**__ and __**C**__'s relationship seems to be smooth sailing. But __**C**__ doesn't know what she got up to in Paris, does he? _

_Fashion Week is still on for another six days. And you know what that means! Free samples and partying from dusk 'til dawn. And if you're not doing that, then that just means you're not one of __**us**__._

_You know you love me,_

_x__oxo Gossip Girl._

* * *

Jenny helped Lily wave off the last few guests while Damon stood near the bar, nursing what appeared to her to be his sixth scotch. She tugged on her mini-dress absently, pulling it down to a more modest length as she shook hands with an old guy. The head of the Bass legal department. He held her hand for a bit too long and looked her up and down creepily. Jenny bit down a shudder and instead replaced it with a smile.

"Thanks for helping out, Jenny," Lily said warmly.

"No problem," Jenny assured her, offering a more sincere smile to her step-mother. Lily glanced over Jenny's shoulder to Damon in the corner.

"Can I finally meet him?" she asked in a hushed voice. Jenny thought for a moment. Six drinks? Was that really wise? She wondered if he could hold his composure long enough to lie, but before she had time to say 'I think I'm just going to put him in a cab', he was at her side with a charming smile.

"You must be Lily Van der Woodsen-Bass-Humphrey," he said in his most sincere and sober voice. "I'm Damon Salvatore."

Lily did that little cringe that always crept to the surface after hearing her three-barrelled surname, courtesy of her three husbands, but her smile didn't falter. Jenny could smell the scotch on his breath, but he was holding himself awfully well. If this was him after six drinks, how much could he have drunk that first night?

"Damon, it's so lovely to finally meet you. I'm surprised that Jenny hasn't brought you up before," Lily smiled and cast a quick glance at her step-daughter.

"I didn't want to jump into anything too soon," Jenny said, trying to sound sincere. But that was her style, wasn't it? Falling in love with the first boy to show her positive attention? Shacking up with drug dealers because it's exciting? Having sex with your step-brother just because you're lonely? She really had been trying to turn it around for the past two years, but that didn't mean that the black marks on her record were going away any time soon.

"Besides, Jenny had no idea how good I looked in a suit," Damon cocked a smile. "I'm sure if she did, she could have invited me to one of your parties weeks ago."

Lily laughed at Damon's show of confidence, clearly charmed by his attitudes. Jenny was tempted to roll her eyes. How was it that he simply entranced everyone like that? It couldn't just be his good looks...

Lily then asked about his family, and he began reciting the whole 'Italy blahblahblah Giuseppe blahblah' over and over again. Jenny briefly wondered how much of it was really true, but Damon was speaking with such conviction and a 'Well, yeah, this is how it went' attitude that it didn't appear to be even slightly false.

"Do you have any siblings?" Lily asked.

"Yes, a brother," he nodded.

"What's his name?"

"Stefan. He's back in Virginia."

When Jenny and Damon left the party to get to the black town car, Damon gave Jenny her coat and opened the car door for her. Jenny didn't say anything, stunned by the show of chivalry. The ride back to Jenny's apartment was quiet, until Damon cleared his throat.

"I think the words you're looking for are 'Thank you'," he chided, cocking an eyebrow at her lazily.

"Thanks, Damon," Jenny said quietly. "Um, you really did me a favour tonight. I won't forget it."

More silence. Too much silence.

* * *

Damon could hear Jenny's heart beating in the back of the car. He could feel each lap of her pulse radiate the air outside of her. He had been drinking heavily all night to repress his hunger for her but it simply hadn't worked. Now he was slightly drunk in the back of the car with her and he didn't have enough self control. But when she said thank you – no matter how forced the sentiment had been – he had scolded himself.

No. She was just a girl who needed a favour.

Damon was about to tell the driver to take him to the Plaza Hotel – where he was staying in the penthouse, because hey, why not? – when his cellphone rang.

"Hello?" he answered slowly.

"Damon?" Elena's voice on the other end was slightly worried. "Are you drunk?"

"Elena, hey," Damon smiled. Jenny cast him a quick glance. Duh. She wasn't expecting him to talk to other girls.

"Stefan, he's drunk," he heard Elena call out across the house, her voice slightly further away from the receiver.

"Elena, I'm fine," Damon assured her. "To what do I owe this honour of a phone call?"

Elena's deep intake of breath over the line was shaky with excitement. "I had to tell you. I just didn't know who else I wanted to tell half as much," Elena admitted.

"What did you want to tell me?" Damon probed, earning him another glance from Jenny beside him.

"Stefan! He proposed to me and I said yes and he's finally agreed to turn me and I really, really want you to be here for that. And Bonnie said she's going to make me a ring, and I'm just so excited I can't keep it in!"

Damon was silent for a second.

"Congratulations," he replied, playing with a loose thread on his shirt. He knew he didn't sound as enthusiastic as Elena wanted, but he couldn't help it. He put it up to being drunk. He always was a depressive drunk. Or an impulsive drunk, but this was hardly the situation to make brash decisions.

Jenny kept her eyes on him as he hung up. Impulsively.

"Who's Elena?"

"My brother's girlfriend," he let out a mirthless laugh. "Or, rather, his fiancé."

Jenny pursed her lips and frowned, her eyebrows (which, he realised, were several shades darker than her hair. He wondered how often she had to bleach her roots...) meeting in the middle of her pale forehead.

"You didn't sound so enthusiastic," Jenny pointed out.

"Don't get me wrong, I love Elena," he said easily, knowing that the gravity behind that four letter word was a lot more than Jenny would think, "and she and Stefan and _perfect_ together," he bit out the word like it was poison, "But..."

"But..." Jenny probed.

"Them getting married is going to ruin her life. It'll kill her," he stated mysteriously with a shrug of his shoulders.

Jenny shrugged with him. "When's the wedding?"

"Knowing them? It'll be soon. They've only been seeing each other for two years. You'd think they'd learn to take things slow," he muttered under his breath.

"You mean like us?" Jenny joked, before she could stop herself. Damon didn't reply. She had just compared this – what they were doing, this joke, this charade between strangers – to a legitimate relationship. He didn't even know _how_ to reply, or what to say. Instead, he watched her nervously fumble for her pack of cigarettes before lighting one and opening the car window.

"Where are you staying?" she asked, exhaling a plume of smoke.

"The Plaza."

The driver nodded when she directed him to the hotel, and the pair didn't speak for the remainder of the journey.

* * *

**Reviews = love for me.**


	4. I'll smoke what you sigh

_Another chapter! Huzzah! Maybe one day people will actually read this. Ha._

_X Alice_

_

* * *

_

Chapter Four: I'll smoke what you sigh

* * *

When Damon had entered his hotel room, he had collapsed on the downy bed and let out an anguished sigh. What the fuck was he doing? He had left Jenny – bitchy, catty, pretty, legs-that-go-on-for-miles _Jennifer Tallulah Humphrey_ – in the car downstairs. The Damon he _used_ to be would have grabbed her by the throat and had his way with her, feeding from the artery in her upper thigh and wiping her mind to mush in the morning. But he couldn't, for more than one reason.

One – he _knew_ Jenny now. She wasn't someone you just played with. She wasn't a Vicki or a Caroline. She was different. Although he wasn't sure how or why, just yet.

Two – he was too fraught to do anything, let alone feed and/or have sex. Elena and Stefan were getting married. And more than that, but his baby brother was going to _turn her_. Stefan had never turned anyone in his life! He was always caught up in the 'moral implications' of it all. But it was real, and it was happening. It wasn't just hypothetical anymore.

Back when Damon was still living in Mystic Falls, he and Elena had had the 'vampire' conversation more than a few times. It usually went the same way, "I don't know. Do you think he'll do it? Maybe I shouldn't ask" etc.

In a burst of frustration, he flipped open his new, paper-thin phone. It chimed to life prettily and he tapped one on speed-dial. Elena.

"Damon?" she answered in a low, angry voice.

"I'm sorry I hung up on you before," he managed to say, his hand over his eyes. What else was he supposed to say?

"I don't understand what your problem is," Elena sighed.

"Elena," Damon said pointedly, getting up off the bed in preparation for a good old fashioned pace around the room, "I don't think you're appreciating the seriousness of the situation..."

"I am _so_ appreciating it," she argued. "I've talked it over with Jenna and Ric and everything and they are totally for it. They know that one lifetime isn't enough when the person you love will live forever."

Damon let out a laugh. "I doubt Ric, of all people, would advocate this."

"Okay," Elena let out a low sigh, "So they weren't exactly jumping for joy at the idea, but they understand."

Damon wiped a hand through his hair in disbelief, before deciding, "Let me talk to Stefan."

"Damon, I don't think that's-"

"Let me. Talk. To Stefan," Damon repeated, his voice low and threatening. Not that he could really do something from 450 miles away, but Elena fumbled with the phone for a bit before handing it over to a new voice.

"Damon," Stefan's voice was broody, and suspicious, as always.

"Are you out of your _fucking mind_?" Damon yelled into the phone. "You're killing her. You are _killing_ the girl you're supposedly in _love_ with. Do you know how fucked up that is? Stefan? Answer me!"

There was silence, and then a sigh from Stefan's end of the line.

"I know what I'm doing."

"Oh, really?" Damon let out a mirthless laugh. "Have you ever turned anyone before? Ever? Because I have and it isn't all peaches and rosemary. They fucking _die_ at your _hands_."

"You think..!" Stefan yelled, before lowering his voice to a whisper, "You think I haven't killed anyone before? I have, Damon."

"Fine," Damon relented. "Get married. Kill her and turn her into a monster. I'm not going to be around to watch it."

"Damon," Stefan said in what he probably assumed would be a soothing tone. "Come on. Don't be ridiculous. Elena... Elena loves you. She really does. And I know you love her, romantically or not-"

"Don't even bring that shit up, you assho-"

"Listen," Stefan interrupted him. "I know you care about her and you're not going to ruin the most important day of her life out of pride."

"Pride?" Damon let out another laugh, slightly more crazed. "You think I'm doing this out of _pride_?"

Stefan's tone was even when he said, "Yes. You want to be the one to turn her. You always have."

The silence hung between the phone lines like a blanket. There was only the buzz of electricity in Damon's ears. He could feel the circuits ticking. He was on high alert. He needed to calm down.

"You're full of shit, Stefan," was all he said, before he snapped the phone shut and threw it against the wall. It made a satisfying crack as the slim metal split into several pieces, falling to the floor. It left a mark on the Plaza's intricate fleur-de-lis wallpaper.

Shit.

* * *

When Jenny awoke the next morning, it wasn't because of the light streaming through the windows, or her alarm going off. No, her phone was the culprit. A Gossip Girl blast.

_**J**__ left with her new leading man last night. But guess who went to bed alone? There's something fishy about this new guy, alright. No way would__** J**__ turn down any guy that good-looking for a late night rendezvous. The only explanation? __**J**__ was the rejectee. Better luck next time, babe! Maybe __**C**__ will be up for some cavorting once he finds __**B**__'s Parisian itinerary..._

Jenny let out a groan of dissatisfaction. It was true that Damon had gone to his place instead of stayed the night at hers, but it had nothing to do with sex or lack of sex! No! It had been about his stupid brother and his stupid fiancé. They put Damon in a bad mood.

Sure. It had nothing to do with the awkward statement that she blurted out.

Us.

Like there even _was_ an 'us' in their duet. Damon did her a favour. And now that the favour was over and done with, so was she. That was depressing. Jenny rolled over in bed and lit her morning cigarette. Maybe _she_ should go to Paris... she might fit in there. Not like in New York where everyone was always trying to dig up dirt about her, one up her, make her feel like trash.

She sighed a long plume of smoke and looked at her thin, pale wrist. Eight o'clock. On a Saturday morning? Gossip Girl really _was_ out to get her.

She flipped through her phone to see if Damon – correction, if _anyone_ – had texted her the night before. No new messages. In a fit of premature desperation, she clicked 'call' on his number, but all she received was an automated 'currently unavailable' message. Damon.

Jenny got out of bed and strolled around her apartment naked. She liked living alone. It was so much better than when she lived in dorms at F.I.T or with her dad in Brooklyn. She had total and complete privacy in her own apartment. Nobody was about to walk in on her as she walked naked around her living room with a cigarette and no shame.

That's why it was almost fortuitous that Damon would walk in right at that moment.

"Good morning," he gave her a smile. It took her a second to register is presence in her doorway – her _open_ doorway (hadn't she locked up after she came in?) – so she stood bemused for a moment before scrambling for a silk slip to put on.

"Shit! Don't you ever knock?" she squealed, pulling the beige slip over her head and fumbling to find her cigarette – which she dropped. If it burned through her samples her Design teacher would cut her throat.

"I did knock," Damon smirked haughtily. "You didn't hear me, and the door was unlocked."

"I was naked," Jenny pointed out, stubbing out her cigarette on the windowsill's ashtray, her back to the intruder.

"I noticed," he smiled as she turned around.

Jenny was about to fume at him about invasion of privacy ("You're as bad as my father!") when she noticed the paper bag and coffee in his hands. It was labelled cheerily with "Breakfast Pastries!" and the coffee was Starbucks, filling her apartment with the scent of freshly ground coffee beans.

"You brought me breakfast," she stated incredulously. It wasn't a question, merely an observation. Why would he bring her breakfast?

"Well, I was going to call and apologise," Damon began, entering her apartment and closing the door with a kick of his feet, "but my phone broke. Suddenly and mysteriously."

When Jenny didn't reply, he continued, "So, I thought the best way to apologise would be to bring you breakfast because I never see you eat much. All you do is pace and smoke and wear too much eyeliner."

"I wear the perfect amount of eyeliner," Jenny defended weakly, glancing over at her overflowing ashtray full of cigarette butts. Maybe he did have a point.

Damon set the breakfast down on her kitchen countertop and Jenny observed him. He was wearing a tight grey T-shirt, a leather jacket and a pair of dark wash jeans. Very stylish. She was tempted to ask whether the shirt was John Varvatos, but decided against it. As if Damon would know anyway.

"Your phone breaking isn't the most mysterious thing around here," she observed. Damon just smiled and sipped his coffee, before handing hers to her. Jenny received it cautiously with a smile. She tucked a strand of hair behind her ear and wondered what a wreck she must look like. Eyeliner smudges, hair all over the place. And still Damon was looking at her like he'd like to do nasty things to her.

Well, you know, she wasn't complaining.

"So," Jenny ventured, sipping her coffee, "I'm sure you have some ulterior motive for bringing me breakfast."

Damon raised his eyebrows suggestively, but Jenny only snorted in response.

"Actually," Damon admitted, "I do."

Jenny cocked an eyebrow, silently asking him to continue.

"I did you a favour, and I'd like the favour returned."

* * *

Damon didn't know _what_ he was doing. It had all happened so fast. The email from Elena saying 'Stefan and Caroline are on their way to see you' had come as a huge shock to his system. Stefan and Caroline? Broody and Slutty? Those were two vampires he was in no mood to see and Elena knew it. Especially after Stefan had the audacity to claim that the only reason Damon was upset was because he wanted to turn Elena. Elena was going to die no matter who her sire was. It didn't fucking _matter_, did it?

But they were coming, and fast. The trip from Virginia to New York was upwards of seven hours, so he had time to fill Jenny in and get her on his side.

And if things didn't go as planned? Well, he could always compel her.

"You're right when you said I was mysterious," he smirked at her. Jenny just shrugged her thin shoulders and continued to nurse her coffee. Damon had got it black, and wondered if she liked it that way. She seemed like the black coffee type, but he wasn't sure.

"I have a secret I need to tell you," he admitted.

"What about this favour?" Jenny cocked her head to the side, her mass of white-blonde hair following suit. She looked so bedraggled and sexy, it was ridiculous.

"In order for you to do me the favour, you need to know the secret," he continued.

Jenny just stared at him expectantly.

Shit. This was going to be harder than he first thought.

"You see this ring?" he tried, lifting his hand up to Jenny's face.

"It's ugly. Whatever," she raised a dark eyebrow and smiled. Damon rolled his eyes.

With a sigh, he moved into the shadowed area of her living room and removed the ring slowly.

"Watch," he instructed. Jenny's deep blue eyes followed him as he reached out into the morning sunlight that streamed through her window.

Instantly, the stinging began. And the sizzling. Damon bit his lip and retracted his hand from the sunlight, watching as the boiled skin healed and mended.

Jenny had put her coffee down. She was staring at him with her eyes so wide he could see the white all the way around her iris. But she didn't move. Her eyebrows simply knotted in her forehead. Damon then replaced his ring and picked up his own coffee. He removed the lid and tilted the cup so that she could see the contents. The thick, deep red blood that he had emptied from the Blood Bank bag that morning swished around, the metallic smell rising up to his nose.

Jenny's mouth fell open.

"What..." Jenny began, before shaking her head and getting up off of her chair. "Are... are you trying to tell me that you're a _vampire_?"

Damon shrugged nonchalantly and took a sip from his cup.

Jenny had the exact expression he was expecting. The expression of someone who's entire reality had just shattered. The panicked expression of someone who had just realised that nightmares were no fantasy and that there were things that really did go bump in the night. Her world had just caved in, and it showed on her face. She took a strangled gasp for air, before letting out a tight laugh.

She swallowed deeply, before attempting to shrug herself, "Well, at least you don't sparkle."

* * *

**Review, por favor**


	5. Nothing left to lose

_First and foremost, to the reviewer who said that I should make Jenny more "like the old Jenny" and less of a "slut who smokes", I have a few things to say to you._

_First of all, thank you for reviewing._

_Second of all, if you want a Jenny/Damon fic where Jenny isn't characterized like this, write it yourself. _

_Third of all, despite the fact that I shouldn't have to justify my characterization to someone who doesn't know how to punctuate their sentences, perhaps I should clarify a few things..._

_The 'old Jenny' doesn't exist anymore. Even on the show, Jenny has reached a level of badassness that defies the norm. The 'old Jenny' has been kicked and scratched and shoved to Hudson. This is where I think her natural progression would take her in terms of her attitude. And, she is a bit of a slut, in case you haven't noticed. Despite only recently losing her virginity to Chuck in the show, she has an instinct to latch on to whoever'll take her, and that's what I've been focusing on. As for the 'smoking' thing, she's still a teenager. Show me a teenager in New York City, especially one with an attitude like Jenny, who doesn't smoke, and I'll give you a cookie._

_I'd add more, but I think that the 'fuck you' is implied._

_Love Always,_

_Alice_

_

* * *

_

Chapter Five: Nothing left to lose

* * *

This was psychotic. Absolutely and completely ridiculous. Jenny's first instinct was to laugh it off. But he had burned in the sun. _Burned_ in the fucking _sun._ And that could only mean one thing. Vampire.

Or, you know, albino. But the ring and the blood... it was all too much.

And yet, you know, it made a lot of sense. Jenny had seen some weird shit in her life. Sure, she lived in New York City, and there were a lot of freaks in New York, but people went missing all the time. And the myths had to come from _somewhere_, didn't they? All myth comes from a grain of truth. And you know what they say. The greatest trick the devil ever pulled was convincing the world he didn't exist.

Not that Damon was the devil. Far from it. Though he did look pretty devilish as he sat with her in her tiny living room, taking a long drag from the cigarette she had lit for him with shaky hands.

"I guess you don't have to worry about the whole lung cancer issue," she mentioned absently, gathering her knees up to her chest as she cat in the big old armchair across from him.

"After about one hundred years, your teeth start to turn yellow," he shrugged and cocked an eyebrow at her. Jenny laughed, and tilted her head to the side to look at him.

"Something tells me that you're not just interested in my bad habits," Damon commented, stubbing out the butt the ashtray Jenny kept on her coffee table. But then he wiggled his eyebrows and added, "or are you?"

Jenny looked away with a small smile on her face.

"You drink human blood," was all she said, unable to look at him as she said it. He let out a low chuckle and she could see him nod out of her periphery.

"Yes. But I don't kill people," he offered. "Much."

Jenny felt her eyes go wide and Damon simply laughed again.

"Hey, at least I'm not like my goody two-shoes brother, Saint Stefan," Damon snorted. "He drinks _animal_ blood. It keeps him alive, but barely. And it also means that any whiff of human blood sends him wild. I know what I am and I don't fight it."

"And what exactly are you?" Jenny ventured. "Are you really dead? Because that just can't be possible."

Damon rolled his eyes. "Magic. It's all magic. I'm like an animal that runs on magic."

Now it was Jenny's turn to snort. She cast Damon an incredulous look.

"Magic?"

"Magic."

"Magic doesn't exist," Jenny assured him, but Damon just ran a hand through his hair and cast her a pointed glance.

"Ring," he held up his hand, the ugly green ring on his middle finger glinting with the intricate family insignia in the sunlight. "Magic."

Still unsure, Jenny stayed quiet. Sure. Magic. And there was a leprechaun at the end of each and every rainbow. Jenny wasn't about to believe everything Damon told her, despite the whole... vampire issue. No. She wasn't _that_ gullible. But curiosity bubbled up inside her stomach and she found herself asking the first question that came to mind.

"How come you didn't drink my blood?" she blurted out. When Damon raised his eyebrows at her, she continued. "You know... when we..."

"Made the beast with two backs?" Damon finished for her, letting a smirk cross his face. "Don't get me wrong. Blood sharing can be incredibly... intimate. If you want it to be. But, I don't know. I didn't feel like it."

Jenny let her legs dangle down off of the large chair. "You didn't _feel like it_?"

Damon snorted. "Well, Chanel Number Five doesn't exactly get my mouth watering. Let me just put it that way."

* * *

Okay. So maybe telling Jenny the truth hadn't been the best idea. She was far too curious, far too unafraid and far too optimistic about this plan. This plan to prove to Stefan and Caroline (and, by proxy, Elena) that he had moved on. And not only had be moved on, but he had moved on with a human!

Okay. So it wasn't the _best_ plan in the world. But afterwards he could compel Jenny to forget the whole ordeal. Compelling her before then would be too obvious to Stefan. He'd be able to sense the brain-deadness and lack of lustre in Jenny's deep blue eyes. And he couldn't have Stefan thinking that he was trying to trick him. Despite the fact he most definitely _was_.

If Damon were to ever have a relationship with a human, it would most definitely not be with a girl like _Jennifer Humphrey_. She was brash and constantly had a sour expression on her face like the world had just spat her out. And she was a designer. Of fashion. And Damon had seen her samples around the apartment – if she ever made menswear, he would steer clear of it. It'd be plaid and grungy and it would have to be paired with eyeliner.

Damon had worn eyeliner in the eighties (his punk phase, which he never spoke about) and he was definitely never going to do it again.

"So," Jenny huffed from behind her closet door as she got changed. "Why me?"

"Because I haven't bitten you, or compelled you before. And you know my secret. And that's all I need."

Jenny poked her head out from behind the door, and Damon could see her bare shoulder and protruding collarbone. What kind of eighteen-year-old had a walk-in-closet in her apartment, anyway? "Compelled? Like, glamoured?"

"You've been watching too much True Blood," Damon narrowed his eyes at her with a smile. Jenny just rolled her eyes and returned to her closet. Over the clacking of hangers and rustling of clothes, he heard Jenny mutter something about him 'not watching enough True Blood', before he could hear her slip into something.

He was surprised at what she was wearing when she finally stepped out from behind the closet door. It was a cream dress that stopped mid-thigh. Versatile, like it could be dressed up or down. Without all of her makeup on she looked almost innocent. Barefoot in a cream dress. Damon suppressed a smile.

"What do you think?" she asked. "I haven't worn this since I was, like, fifteen."

Damon nodded. Perfect.

* * *

Jenny dared a glance at Damon as he chatted away on her cellphone. He had to borrow it to call his brother because his phone had 'mysteriously broken', and was arguing heatedly with the person on the other end. She didn't know why. They were counting on his brother (Stefan, wasn't it?) and some girl (named Karolina or whatever) to show up so the charade could begin. But Jenny supposed it was to keep up appearances.

"Fine," Damon seethed convincingly into the receiver of Jenny's iPhone. "Come. But I'll have you know that you'll have to deal with some... company. No. No, not like that. Well, sort of. No I am not! She's... yes. She knows. No, I haven't. What do you take me for? Name one time I've done that... okay, name another. Yes. Yes, I'll be there. Fine. See you then."

Damon hung up with a pleased expression on his face. "They're almost here. About half an hour away."

Jenny nodded and touched her neck self-consciously. It had been a long time since she'd worn her hair up off her shoulders. But Damon insisted that it would show her scar-less jugular and that it also made her look less, well, his words had been "less of a train-wreck". But whatever.

The pair made their way to the restaurant where they were meeting their visitors. Damon pulled out Jenny's chair before she sat down and she repressed a blush at the act of chivalry. In New York, people so rarely were even remotely polite, let alone chivalrous.

"So," Damon told her after they had ordered. "When Stefan and Caroline get here, you smile and get up and gush about how much you've heard about them."

Jenny rolled her eyes. Damon had ordered ravioli. Did he even eat? He had eaten a Danish that morning but that was before the whole secret thing was exposed and she assumed he was just keeping up his 'Human' act.

"Fine," Jenny conceded. "Anything else?"

Damon's eyes shot wide, as if he remembered something, and he reached into his jacket pocket. He pulled out what looked like a balled-up tissue, but when he unwrapped it, an antique charm bracelet was in the folds.

"Put this on," he ordered.

Jenny frowned, but took the bracelet gingerly with two long, pale fingers. "Why?"

"You see that big round charm?" he asked. Jenny looked at the bracelet – there was an intricate ball charm in between a heart charm and an Egyptian eye charm.

"Yeah, what about it?"

"Inside it is this herb called vervain," Damon explained. "It's poisonous to vampires. If you have it anywhere on you or in you, a vampire can't compel you. It'll be more proof. And," he added, as if it were an afterthought, "it means that Caroline and Stefan can't compel you into ratting out this little game."

Jenny nodded as she fiddled with the intricate little clasp on the old bracelet. With a sigh, Damon reached over and did up the clasp over her wrist, his cool fingers brushing over the inside of her wrist gently. Absently, after he did up the clasp, he traced a blue vein on her wrist, causing Jenny to shiver.

"Sorry," he shook his head, as if breaking out of a trance.

Caroline and Stefan arrived at the same time as Jenny and Damon's food. Damon nudged her under the table and cocked his head toward the door. Jenny glanced up at them and her heart started to race. Damon's brother was handsome, and looked younger than Damon by several years. So did his companion, a blonde girl with dark, penetrating eyes. Caroline, she figured. Why not send Elena? That seemed weird.

But Jenny did as she was told and leapt up off of her seat and went up to greet them both. With a huge smile made even larger by nerves, she skipped over to them in her ballet flats.

"Oh wow, hi," she said quickly. "You must be Stefan and Caroline."

Stefan smiled, but frowned, as if he were amused and confused at the same time. Caroline's eyebrows shot up in a surprised expression, her mouth a little bit agape.

"Who are you?" Caroline asked tersely.

"How silly of me!" Jenny gushed, "I know all this stuff about you, and you know nothing about me! I'm Jenny, Damon's... friend. Come, come, sit!"

With a quick glance at each other, Stefan and Caroline shrugged and followed Jenny to the table where Damon was eating his mushroom ravioli with a pleased smile on his face.

* * *

**Reviews = love**


	6. Light me up when I'm down

Warning: this chapter contains rather explicit sex that should probably not be read by anyone. It is way too steamy and pleasantly erotic.

_Love Alic__e_

_

* * *

_

Chapter Six: Light me up when I'm down

* * *

Jenny was absolutely perfect.

She was smiling and bubbly and conversational and so... not like her usual grumpy self. Although Damon couldn't exactly say that he knew who she really was, seeing as their relationship revolved around secrets and one drunken night together. The cherry on the cake? Stefan and Caroline were so uncomfortable with it. Not Jenny (no, she was charming and vivacious and they took to her personality immediately), but rather the idea that a new human knew about vampires. Oh yes. They were extremely uncomfortable with it.

"So," Jenny said, taking a sip of her diet coke. "Damon tells me that you and Elena are engaged?"

Stefan blinked. "Uh. Yes, only recently. That was kind of the point of this trip, actually."

"Damon won't come," Caroline said plainly, casting a glare at the dark haired vampire across the table.

"I don't want to watch you ruin her life," Damon admitted flippantly. "Or end it."

He looked at Jenny briefly as understanding crossed her face. Of course, that was the one part of the situation he failed to include. The whole 'turning Elena' thing was still a sore spot. But she caught on, and turned to face Stefan with a concerned expression on her face.

"You're going to turn her?" she asked in a low voice.

Stefan ground his teeth together, which was a pleasant sight for Damon. He loved to watch Stefan squirm.

"Listen, I know you and Damon probably haven't discussed the possibility of, well, eternal companionship," Stefan replied, "but Elena and I think it's the right thing to do."

"We have," Jenny interjected suddenly. "Talked about it, I mean."

Damon frowned and looked at Jenny with an amused expression. What was she playing at? This wasn't in the handbook.

"You... you have?" Caroline cast a look at Damon.

"If we decide it's the right thing to do," Jenny began, looking at Damon with an expression he could only describe as sincerity, "we're going to wait until I'm twenty-one."

"Well," Stefan countered, without even properly registering the weight of Jenny's statement, "He's physically twenty-four. I'm seventeen, technically. Elena doesn't want to be older than me."

"Yeah," Caroline snorted. "When she hits the one hundred year mark, she might start to get self-conscious."

There was silence as Jenny daintily sipped her diet coke in an attempt to be casual.

"I think," Jenny began, "that it's a good idea."

* * *

Damon's glare hit her like ice down her dress. Cold, and shocking and ... wait. Arousing? God, she really needed to get over him, and quickly, otherwise she might jump him any minute.

"You do?" he asked incredulously, icily.

"It's not really my decision," Jenny stammered, trying to regain her grip after being dealt such a hefty glare. "But if they're married, then..."

"Elena has friends and family, despite the fact that those she's closest to support her. Eventually they'll realise she's not getting any older," Damon countered angrily. He turned to Stefan, "What are you going to do? Fake her death? That's the plan for Caroline, isn't it? So mommy dearest won't find out?"

Caroline blinked up at the ceiling, as if blinking back tears.

"I'm your entire_ fault_, anyway," Caroline bit out. "I mean, God, regardless of Katherine, it was your blood that turned me, Damon. The way I am, the way my mom is, it is your fault."

Jenny suddenly felt like a much bigger story overlapped hers. She felt crushed by it. Maybe that was all she was – a footnote in Damon's un-life. Just a chapter in a much larger tale. Who was Katherine? And what exactly was his relationship with Elena? Jenny's eyes went wide as she realised: despite knowing the crucial factor about Damon (vampirism. Duh.) she knew nothing at all about him.

Her reverie was broken by her phone buzzing.

_Gossip Girl here, your one and only source into the scandalous lives of Manhattan's elite._

_Spotted: __**Little J**__ at Butter with __**Tall Dark and Handsome**__, sharing a plate of ravioli with some enticing new strangers. What is it with __**J**__ and gorgeous, pale people? And why is the foursome whispering so much? __**J**__ is many things, but subtle is not one of them. I'm sensing another guerrilla fashion show, circa 2008. Or something equally delicious. Whatever it is, I'll be there._

_Will you?_

_You know you love me, _

_xoxo Gossip Girl_

Jenny groaned as she stared at her phone, ignoring the heated whispering between Caroline and Damon. She could hear fragments of "Katherine blahblah" and "Your fault blahblah", but despite everything, Gossip Girl was her biggest worry. Ha. She supposed that said something about her, didn't it? Sitting at a table with blood sucking monsters and she's more worried about an anonymous gossip mogul.

Pathetic.

"Jenny, what do you think?" Damon asked suddenly, turning to her with fire in his bright blue eyes.

"W-what do I think about what?" she asked, tucking her phone under the table.

Damon's eyes followed her hands. "What are you looking at?"

"It's nothing, really," she insisted, quickly. But Damon was too quick. He had already snatched up her phone and was looking at it with definite interest.

"Gossip Girl?" he raised an eyebrow at her disbelievingly.

Stefan and Caroline were silent with interest, watching as Damon scrolled down the phone swiftly.

"Little J, Little J..." he read aloud. "You have a stalker."

"She's not a stalker," Jenny defended, snatching her phone back. "She's a gossip columnist."

"_You're_ in a gossip column?" Caroline asked tersely. Jealous, much?

"It's a Manhattan thing. It's this anonymous girl who was a few years ahead of me at High School. She's super rich and everyone sends her tips and it's really quite ridiculous when I admit it out loud," Jenny babbled.

"Gossip," Stefan murmured. "You mean, like rumours?"

"She's trying to figure out what the mystery about my new friends is," Jenny admitted, flashing them a picture. It was taken from a few tables away. It was of all four of them, leaning in over the table, whispering.

"As if they'll guess," Caroline scoffed and sipped her red wine, rolling her dark eyes defiantly.

Yeah. As if.

* * *

"So, do you think we convinced them?" Jenny asked as they drove back to Damon's hotel. He could feel her heart beating around the back of the cab, but wasn't sure if it was adrenaline from lying so swiftly or nerves about going back to his place. He had no wicked intentions. None at all.

He simply thought she deserved an explanation, and he needed some blood.

"Of course we did," Damon replied breezily. "You're quick witted, I'll give you that much."

Jenny sighed a shaky breath of relief. "I thought I was going to crap my pants when the whole wedding thing came up."

And with that, all of her previous charm went out the window. Lovely.

"Yeah, well, if you hadn't agreed with Saint Stefan then maybe it wouldn't have had such an adverse affect on you," Damon shrugged, looking out the window as Manhattan flew past him in a blur of lights. City that never sleeps, indeed.

"So you're in love with Elena," Jenny muttered suddenly. "I get it. But that doesn't mean you should stop them from doing what they've got to do."

Damon whipped his head around so fast that it gave Jenny a shock.

"I am _not_ in love with Elena."

He tried to sound as absolutely and positively sure of himself as possible. He wasn't. He _wasn't_. Not any more, anyway. Not that he ever was. No. Never.

"She is self-righteous and holier-than-thou and... and," Damon continued, "she and Stefan are _perfect_ for each other."

"Yeah, I believe you said something like that before," Jenny said, a small smirk on her face. God. Was he really so flustered that she could make fun of him like this? Elena was a sore spot but not _that_ much of a sore spot.

"You want to know the whole story?" Damon asked. "Top to bottom, back to front, and all that jazz?"

Jenny bit her lip and nodded, her eyes shining with genuine sincerity.

"It's a long one," he warned.

Jenny smiled. "I don't have any classes tomorrow. I've got time."

[insert]

By the time Damon had finished the story, the sun had been up for three hours and Jenny had bags under her eyes the size of saucers. It had surprised her how the night had panned out. He invited her in, offered her a drink. She had sipped wine and he had sipped O Positive and he had sat her down and told her everything. From page one to one-hundred, from 1865 to present, from Katherine to Elena.

It was exhausting to just hear about it.

"Now you know everything about me," he finished with as he opened up the curtains and let a long stream of sunlight hit his face. Jenny stared at him as the light cast his visage in strange shadows, catching on his cheekbones and making his bright blue eyes sparkle. God, he was perfect, wasn't he?

Only he wasn't. She knew that now. He was far from it.

"Why even bother telling me?" she asked. "I'm just a pawn in your plan to get Elena back, anyway."

Damon turned to face her, his face etched with confusion.

"No, you're not," he looked away.

"But everything you've described to me," Jenny argued, her head spinning from lack of sleep and lack of nicotine and lack of caffeine, "it all points to you wanting Elena for yourself."

"You'd think so," Damon said softly. "But you'd be wrong."

"But you love her."

"I do," he admitted. "But I'm not _in_ love with her. Not anymore. Being in love requires some form of reciprocal feelings. And she's one hundred and ten per cent Stefan's."

"Just like Katherine was," Jenny added.

"What are you, my shrink?" Damon smirked at her before sitting opposite her in the dining room.

Jenny ran a hand through her long, somewhat tangled blonde hair.

"I need a shower," she groaned.

"Help yourself," Damon nodded in the direction of the bathroom. Jenny got herself up and locked herself in. Damon's few toiletry items littered the basin and there was shampoo and conditioner in the shower. Jenny undressed and turned on the hot water, before taking a look at herself in the mirror.

Her concave hips were like twin peaks in her flesh, and she could see the soft outline of her rips under her pale skin. Jenny had always been thin, but this year it had taken a turn for emaciated. She needed a cheese burger. Maybe she'd ask Damon to call room service once she'd washed her hair...

* * *

Damon heard the shower turn off and Jenny dry herself off with a towel. Even through the door he could hear her wipe the condensation off of the mirror and sigh. She emerged, face raw and wet, hair up in a white towel, wrapped in one of the Plaza hotel's white bath robes.

Silently, Damon handed her a shirt to put on and turned away as she changed into it.

"I'm kinda starving," Jenny admitted to him. Damon turned back to face her. She was wearing nothing but the large black men's shirt, and was twisting her hair away from her slim, pale neck. Her lips were full and pouty with moisture, and her endlessly long legs stretched to the floor like twin pillars of marble.

Damon narrowed his eyes and her and bit his lip. "Me too."

Jenny barely had time to take a breath before Damon had lowered his mouth onto hers. She smelled of his body wash and shampoo, clean and hot and moist like humid mist. Jenny moaned into his mouth and placed her arms over Damon's shoulders for support as he lifted her to the bed. Her bare legs wrapped around him and he felt up her thigh slowly, caressing the taught flesh of her curved hips. Jenny bit his lip briefly and ran her hand through his hair, gripping tight as his hand found its way to her moist centre.

Jenny's gasps and moans as he played with her were delicious. She even whimpered at one point and muttered something that sounded like 'Please, please'.

Obliging her, Damon lifted his shirt off of her body and let her lay naked beneath him, her wet hair curling on the cushion underneath her. Damon removed his own shirt as Jenny undid his belt buckle and threw it to the side. He caught her staring at the V of his hips that pointed towards his engorged member, her mouth slightly agape.

He lowered his mouth onto hers once more, running one free hand down her body as he pulled down his pants with the other. His thumb brushed over her left nipple, back and forth, playing with it. It was puckered and erect as he lowered his head to swipe his tongue over it, eliciting a gasp from Jenny.

"Stop," she whimpered. "Stop playing. I want you."

That was all the direction he needed. Damon eased himself into Jenny's tight opening, groaning with pleasure at the action. Jenny's long leg was wrapped around his naked hip, and he propped her and to thrust in even deeper. Jenny grabbed his neck and pulled his mouth down to meet hers. He glided in and out of her slowly as their mouths battled one another for dominance. As he thrust, he placed one hand on her hip and the other on her pert breast, teasing it softly.

Had she been this tight the night they first had sex? Because she was really tight. He didn't remember her being _this_ tight. Though, he didn't remember much at all.

The hand playing with her breast travelled down slowly and found the bud of nerves at her centre. Jenny gasped into his mouth as he brushed over it casually with his forefinger while maintaining a smooth rhythm of thrusts. She moaned into his ear, becoming breathless. That was one perk of being a vampire, Damon surmised. You never became too breathless to kiss during sex.

But the sounds of her breathing were just making him more aroused, and he could feel himself ready to blow. Not now, Damon chided himself. Not yet.

Damon lifted up Jenny's light frame and turned so she was on top. He was sitting up, though, so he could still thrust if she was too tired to ride him. But Jenny arched her back and met his thrusts with equal enthusiasm, whimpering and moaning and whispering sentences that made no sense.

"Fuck I... oh fu... mmm... Damon," she moaned in a low, breathy voice. Damon leant forward and captured her mouth again, roughly. While she was preoccupied with his tongue, his hand crept to her clit again and rubbed it firmly.

"Oh god," she gasped, pulling away. Her eyes met his, and he could see it – she was going to come.

"I'm coming," she urged him, riding him harder. He toyed with her pleasure bud with one hand, and with the other rubbed one erect nipple. He needed to get her to come before him – it was always something he simply _had _to do. It wasn't courtesy, it was a matter of pride. Knowing that you could send a woman to the endless planes of ecstasy without 'needing' anything in return was very ego boosting. Not that his ego _needed_ boosting.

Jenny gasped and her tight walls clenched around him as her orgasm rocked her body. Damon couldn't hold it, and he came with her in an explosion of muttered expletives which Jenny muffled with her mouth against his in a long, deep kiss. Her hands ran firmly through his hair as she rode off the last of her climax. She broke away from him and looked him in the eye. The pleasure from the recent orgasm was still on her face, and she smiled broadly at him.

"Great," she said breathlessly, sarcastically. "Now I have to shower _again_."

Hey, Damon thought. He could always join her...

* * *

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